Organic light emitting device

Abstract

The present specification relates to an organic light emitting device including: an anode; a cathode; an emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the emitting layer and the anode; and a second organic material layer disposed between the emitting layer and the cathode, wherein the first organic material layer comprises a compound of Chemical Formula 1, the emitting layer comprises a compound of Chemical Formula 2, the second organic material layer comprises a compound of Chemical Formula 3, and Chemical Formula 1 and Chemical Formula 3 satisfy any one or more of [Formula 1] to [Formula 3].

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2020-0015452, filed with the Korean Intellectual Property Office on February 10, 2020, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to organic light-emitting devices. Background Technology

[0003] Organic light emission (OLED) generally refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices typically have a structure comprising an anode, a cathode, and an organic material layer between them. Here, the organic material layer is usually formed as a multilayer structure of different materials to improve the efficiency and stability of the OLED. For example, the organic material layer can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an OLED structure, holes and electrons are injected into the organic material layer from the anode and cathode, respectively. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons return to the ground state.

[0004] There is a continued need to develop new materials for such organic light-emitting devices.

[0005] Public content

[0006] Technical issues

[0007] This specification is intended to provide information on organic light-emitting devices.

[0008] Technical solution

[0009] One embodiment of this specification provides an organic light-emitting device, the organic light-emitting device comprising: an anode; a cathode; a light-emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the light-emitting layer and the anode; and a second organic material layer disposed between the light-emitting layer and the cathode, wherein the first organic material layer comprises a compound represented by the following chemical formula 1, the light-emitting layer comprises a compound represented by the following chemical formula 2, and the second organic material layer comprises a compound represented by the following chemical formula 3.

[0010] Furthermore, chemical formula 1 and chemical formula 3 satisfy any one or more of the following formulas [1] to [3].

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] L1 and L2 may be the same or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group.

[0015] Ar1 and Ar2 may be the same as or different from each other, and each is independently deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group, and

[0016] R1 to R16 may be the same as or different from each other, and each may be hydrogen or deuterium; or adjacent groups in R1 to R8 may be bonded to each other to form substituted or unsubstituted rings.

[0017] [Chemical Formula 2]

[0018]

[0019] In chemical formula 2,

[0020] L3 and L4 may be identical or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group.

[0021] Ar3 and Ar4 may be identical or different from each other, and each is independently deuterium; or aryl groups, substituted or unsubstituted, and

[0022] T1 through T8 may be the same as or different from each other, and each is independently hydrogen; deuterium; or substituted or unsubstituted aryl groups.

[0023] [Chemical Formula 3]

[0024]

[0025] In chemical formula 3,

[0026] At least one of G1 to G18 is -L5-Ar5, and the remainder is hydrogen, or G1 and G18 are connected by -L51- to form a substituted or unsubstituted ring.

[0027] L5 is a direct bond; or a substituted or unsubstituted aryl group.

[0028] Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0029] L51 is O; or S.

[0030] [Formula 1]

[0031] IE L1 |<IE LA |

[0032] [Equation 2]

[0033] E s1 >E s3

[0034] [Formula 3]

[0035] E T1 >E T3

[0036] In equations 1 to 3,

[0037] E L1 This refers to the LUMO energy level (eV) of the compound represented by chemical formula 1.

[0038] E L3 This refers to the LUMO energy level (eV) of the compound represented by chemical formula 3.

[0039] E s1 This refers to the singlet energy (eV) of the compound represented by chemical formula 1.

[0040] E s3 This refers to the singlet energy (eV) of the compound represented by chemical formula 3.

[0041] E T1 This refers to the triplet energy (eV) of the compound represented by chemical formula 1, and

[0042] E T3 This refers to the triplet energy (eV) of a compound represented by chemical formula 3.

[0043] Beneficial effects

[0044] An organic light-emitting device according to one embodiment of this specification contains a compound of formula 1 between the light-emitting layer and the anode, a compound of formula 2 in the light-emitting layer, and a compound of formula 3 between the light-emitting layer and the cathode, thereby achieving a low driving voltage and improved light efficiency. Attached Figure Description

[0045] Figure 1 and Figure 2 An example of an organic light-emitting device according to one embodiment of this specification is shown.

[0046] Figure Labels

[0047] 1: Base

[0048] 2: Anode

[0049] 3: First organic material layer

[0050] 4: Emissive layer

[0051] 5: Second organic material layer

[0052] 6: Cathode

[0053] 7: Hole injection layer

[0054] 8: Hole transport layer

[0055] 9: Electron blocking layer

[0056] 10: Hole-blocking layer

[0057] 11: Electron Injection and Transport Layer Detailed Implementation

[0058] This instruction manual will be described in more detail below.

[0059] In this specification, unless otherwise stated to the contrary, the description that a part "includes" certain constituent elements means that it may also include other constituent elements, and does not exclude other constituent elements.

[0060] In this specification, the description of a component being arranged "on" another component includes not only the case where one component is in contact with another component, but also the case where there is another component between the two components.

[0061] In this specification, the term "layer" has the same meaning as "film" primarily used in the art, and refers to a coating covering a target area. There is no limitation on the size of a "layer," and layers can have the same or different dimensions. According to one embodiment, the size of a "layer" can be the same as the entire device, can correspond to the size of a specific functional area, or can be as small as a single subpixel.

[0062] In this specification, the meaning of a specific material A being contained in layer B includes both of the following: i) one or more types of material A being contained in a layer B, and ii) layer B being formed as one or more layers, and material A being contained in one or more layers of layer B which are multi-layered.

[0063] In this specification, the meaning of a particular material A being contained in layers C or D includes all of the following: i) being contained in one or more layers of one or more layers C, ii) being contained in one or more layers of one or more layers D, or iii) being contained in each of one or more layers C and one or more layers D.

[0064] In this specification, "or" means inclusive "or", not exclusive "or". For example, condition A or B satisfies any of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0065] In this specification, "mixture" or "mixture material" means comprising two or more types of materials. "Mixture" or "mixture material" may include, but is not limited to, a homogeneous and / or non-homogeneous mixed state, a dissolved state, a homogeneous and / or non-homogeneous dispersed state, etc.

[0066] Unless otherwise defined in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While methods and materials similar to or equivalent to those described herein may be used to implement or experiment with embodiments of this disclosure, suitable methods and materials will be described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety; however, in the event of conflict, the definition in this specification shall prevail unless specifically cited. Furthermore, materials, methods, and examples are for illustrative purposes only and do not limit this specification.

[0067] Examples of substituents in this specification are described below; however, substituents are not limited thereto.

[0068] In this instruction manual, This refers to the connection site.

[0069] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and there are no restrictions on the position of substitution, as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0070] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium; halogen group; hydroxyl group; cyano; nitro; alkyl; cycloalkyl; alkoxy; alkenyl; haloalkyl; silyl; boron; amino; aryl; and heteroaryl, or substituted with two or more substituents linked together from the substituents exemplified above, or without substituents.

[0071] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is connected to another substituent. For example, the connection of two or more substituents may include the connection of phenyl and naphthyl groups to form substituents. Furthermore, the connection of three substituents includes not only the sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) with (substituent 1). For example, phenyl, naphthyl, and isopropyl groups can be connected to form substituents. The same rules described above apply to cases where four or more substituents are connected.

[0072] In this specification, examples of halogen groups may include fluorine, chlorine, bromine, or iodine.

[0073] In this specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0074] In this specification, cycloalkyl groups are not particularly limited, but preferably have 3 to 30 carbon atoms. Specific examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc.

[0075] In this specification, the alkoxy group can be linear, branched, or cyclic. There is no particular limitation on the number of carbon atoms in the alkoxy group, but it is preferably 1 to 30. Specific examples may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0076] In this specification, the alkenyl group can be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0077] In this specification, alkyl haloide means, in the definition of alkyl, that the hydrogen of the alkyl group is replaced by at least one halogen group.

[0078] In this specification, there are no particular limitations on the aryl group, but it is preferred to have 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0079] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of monocyclic aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, etc.

[0080] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of polycyclic aryl groups may include naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, finadeninyl, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0081] In this specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0082] When the fluorene group is substituted, it may include However, the structure is not limited to this.

[0083] In this specification, "adjacent" groups may mean a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that substitutes for the atom substituted by the corresponding substituent. For example, two substituents in an ortho position of a benzene ring and two substituents on the same carbon atom of an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0084] In this specification, a heteroaryl group is a group comprising one or more non-carbon atoms (i.e., heteroatoms), and specifically, heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phenthia Base, Fen Zincazinyl, phenothiazinyl, dihydroindocarbazolyl, spirofluorenyl succinyl, spirofluorenyl thiophene, etc., but not limited to these.

[0085] In this specification, silane can be alkylsilane, arylsilane, heteroarylsilane, etc. Examples of alkyl groups being used as alkyl silanes, examples of aryl groups being used as aryl silanes, and examples of heteroaryl groups being used as heteroaryl silanes.

[0086] In this specification, the boron group can be -BR 100 R 101 R 100 and R 101 They may be the same as or different from each other, and may be independently selected from hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms. Specific examples of boryl groups may include, but are not limited to, trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc.

[0087] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino, although not particularly limited thereto, but the number of carbon atoms is preferably 1 to 30. Specific examples of amino groups may include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc.

[0088] In this specification, N-alkylarylamine means that the N of the amino group is replaced by an alkyl or aryl amino group. The alkyl and aryl groups in N-alkylarylamine are the same as those in the examples of alkyl and aryl groups described above.

[0089] In this specification, N-arylheteroarylamine means that the N of the amino group is replaced by an aryl or heteroaryl amino group. The aryl and heteroaryl groups in N-arylheteroarylamine are the same as those in the examples of aryl and heteroaryl groups described above.

[0090] In this specification, N-alkylheteroarylamine means that the N of the amino group is replaced by an alkyl or heteroaryl amino group. The alkyl and heteroaryl groups in N-alkylheteroarylamine are the same as those in the examples of alkyl and heteroaryl groups described above.

[0091] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups or substituted or unsubstituted dialkylamine groups. The alkyl group in an alkylamine group can be linear or branched. An alkylamine group containing two or more alkyl groups can include linear alkyl, branched alkyl, or both linear alkyl and branched alkyl. For example, the alkyl group in an alkylamine group can be selected from examples of the aforementioned alkyl groups.

[0092] In this specification, examples of arylamines include substituted or unsubstituted monoarylamines, or substituted or unsubstituted diarylamines. The aryl group in an arylamine can be a monocyclic aryl or a polycyclic aryl. An arylamine containing two or more aryl groups can comprise a monocyclic aryl, a polycyclic aryl, or both. For example, the aryl group in an arylamine can be selected from the examples of the aryl groups described above.

[0093] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines, or substituted or unsubstituted di-heteroarylamines. Heteroarylamines comprising two or more heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or both monocyclic and polycyclic heteroaryl. For example, the heteroaryl groups in a heteroarylamine may be selected from the examples of heteroaryl groups described above.

[0094] In this specification, "two adjacent substituents bonded to each other to form a ring" means that adjacent groups bonded to each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0095] In this specification, the term "ring" in substituted or unsubstituted rings formed by bonding together means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0096] In this specification, the hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of aromatic and aliphatic hydrocarbons, and can be selected from examples of cycloalkyl and aryl, the difference being that the hydrocarbon ring is not monovalent.

[0097] In this specification, a heterocycle comprises one or more non-carbon atoms (i.e., heteroatoms), and specifically, heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. Aromatic heterocycles may be selected from examples of heteroaryl groups, the difference being that the aromatic heterocycle is not monovalent.

[0098] In this specification, aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles may include ethylene oxide, tetrahydrofuran, and 1,4-dioxane. Alkane, pyrrolidine, piperidine, morpholine, oxepane, azokane, thiokane, etc., but not limited to these.

[0099] In this specification, arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl can be applied to arylene, the difference being that each arylene is a divalent group.

[0100] In this specification, heteroaryl refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl can be applied to heteroaryl, the difference being that each heteroaryl is a divalent group.

[0101] An organic light-emitting device according to one embodiment of this specification includes: an anode; a cathode; a light-emitting layer disposed between the anode and the cathode; a first organic material layer disposed between the light-emitting layer and the anode; and a second organic material layer disposed between the light-emitting layer and the cathode, wherein the first organic material layer contains a compound represented by chemical formula 1, the light-emitting layer contains a compound represented by chemical formula 2, and the second organic material layer contains a compound represented by chemical formula 3; and chemical formulas 1 and 3 satisfy any one or more of [Formula 1] to [Formula 3]. When chemical formulas 1 and 3 satisfy any one or more of [Formula 1] to [Formula 3], excellent luminous efficiency is achieved in the organic light-emitting device.

[0102] An organic light-emitting device according to one embodiment includes a compound of Formula 1 between the anode and the light-emitting layer (i.e., in a first organic material layer), a compound of Formula 2 in the light-emitting layer, and a compound of Formula 3 between the cathode and the light-emitting layer (i.e., in a second organic material layer). By including the compound of Formula 1 in the first organic material layer of the organic light-emitting device, hole injection and transport become faster, and the transport of charge carriers to the light-emitting layer is maximized, which improves the efficiency of the light-emitting layer. By including the compound of Formula 3 in the second organic material layer, the efficiency of the light-emitting layer can be improved by promoting electron injection and transport to the light-emitting layer, and by including the compound of Formula 2 in the light-emitting layer, the mobility of electrons and holes transported to the light-emitting layer is enhanced, and structural properties that improve molecular stability are obtained. Therefore, a device with low voltage and high efficiency can be obtained.

[0103] According to one embodiment of this specification, the first organic material layer is configured to contact the light-emitting layer.

[0104] According to one embodiment of this specification, the first organic material layer includes an electron blocking layer, and the electron blocking layer contains a compound represented by chemical formula 1.

[0105] According to one embodiment of this specification, the light-emitting layer contains a dopant.

[0106] According to one embodiment of this specification, the light-emitting layer comprises a fluorescent dopant.

[0107] According to one embodiment of this specification, the fluorescent dopant may include arylamine-based dopant, boron-based dopant, and mixtures thereof.

[0108] As arylamine-based dopants and boron-based dopants, those used in the art can be used without limitation.

[0109] According to one embodiment of this specification, the light-emitting layer is a single layer.

[0110] According to one embodiment of this specification, the dopant is a blue dopant.

[0111] According to one embodiment of this specification, the light-emitting layer is a blue light-emitting layer.

[0112] According to one embodiment of this specification, the maximum emission wavelength (λ) of the organic light-emitting device in the emission spectrum is... 最大 The wavelength range is 400nm to 470nm.

[0113] According to one embodiment of this specification, the light-emitting layer further comprises a compound different from the compound represented by chemical formula 2.

[0114] According to one embodiment of this specification, the light-emitting layer comprises two or more types of hybrid bodies, and one or more of the two or more types of hybrid bodies comprises a compound represented by chemical formula 2.

[0115] According to one embodiment of this specification, the light-emitting layer comprises two or more types of mixed bodies, and at least one of the two or more types of mixed bodies comprises a compound represented by chemical formula 2, and the remainder comprises compounds different from the compound represented by chemical formula 2.

[0116] At least one of the two or more types of mixed bodies comprises a compound represented by Formula 2, and anthracene-based bodies used in the art may be used without limitation as the remainder, provided they differ from Formula 2; however, the remainder is not limited thereto.

[0117] An organic light-emitting device using two or more hybrid substrates according to one embodiment of this specification aims to improve device performance by combining the advantages of each substrate. For example, when two types of substrates are mixed, an organic light-emitting device with high efficiency, low voltage, and long lifetime can be manufactured by mixing a type of substrate with high efficiency and low voltage and a type of substrate with long lifetime.

[0118] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant.

[0119] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, and comprises a compound represented by chemical formula 2 as the host and a fluorescent dopant as the dopant.

[0120] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, comprising two or more types of mixed hosts as the host. At least one of the two or more types of mixed hosts comprises a compound represented by Chemical Formula 2, and the remainder comprises compounds different from the compound represented by Chemical Formula 2, and includes a fluorescent dopant as the dopant.

[0121] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, and the light-emitting layer comprises a host:dopant in a weight ratio of 99.9:0.1 to 80:20.

[0122] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, and the light-emitting layer comprises a host:dopant in a volume ratio of 99.9:0.1 to 80:20.

[0123] According to one embodiment of this specification, one or more organic material layers are included between the second organic material layer and the light-emitting layer. The organic material layers include hole-blocking layers.

[0124] According to one embodiment of this specification, one or more organic material layers are included between the second organic material layer and the cathode. The organic material layers include an electron injection layer.

[0125] According to one embodiment of this specification, the second organic material layer includes an electron transport layer, and the electron transport layer contains a compound represented by chemical formula 3.

[0126] According to one embodiment of this specification, the second organic material layer includes an electron injection and transport layer, and the electron injection and transport layer contains a compound represented by chemical formula 3.

[0127] According to one embodiment of this specification, the second organic material layer comprises a compound represented by chemical formula 3, an organoalkali metal complex compound, and mixtures thereof. Examples of organoalkali metal complex compounds may include, but are not limited to, lithium quinoline and aluminum quinoline, and the organoalkali metal complex compound is included in an amount of 10% to 90% by weight, and preferably 30% to 70% by weight, relative to the material of the organic material layer.

[0128] In this specification, "energy level" refers to the magnitude of energy. Therefore, an energy level should be interpreted as the absolute value of the corresponding energy. For example, a low or deep energy level means the absolute value of the increase in the negative direction from the vacuum energy level.

[0129] In this specification, HOMO (Highest Occupied Molecular Orbital) refers to the molecular orbital function in the region where electrons have the highest energy in the bonding region, and LUMO (Lowest Unoccupied Molecular Orbital) refers to the molecular orbital function in the region where electrons have the lowest energy in the antibonding region. The HOMO energy level refers to the distance from the vacuum level to the HOMO. Similarly, the LUMO energy level refers to the distance from the vacuum level to the LUMO. The structure needs to be determined to understand the electron distribution in the molecule and to understand optical properties. Furthermore, depending on the charge state of the molecule, the electronic structure exhibits different structures in neutral, anionic, and cationic states. Although energy levels in neutral, cationic, and anionic states are all important for driving mechanisms, the HOMO and LUMO in the neutral state are generally considered important properties. To determine the molecular structure of a chemical substance, density functional theory (DFT) is used to optimize the input structure. For DFT calculations, the BPW91 calculation method (Becke exchange and Perdew correlation-correlation functionals) and the DNP (double numerical basis set including polarization functionals) basis set are used. The BPW91 calculation method is described in “ADBecke, Phys. Rev. A, 38, 3098 (1988)” and “JP Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992)”, and the DNP basis set is described in “B. Delley, J. Chem. Phys., 92, 508 (1990)”.

[0130] Biovia's "DMol3" package can be used for calculations using density functional theory. When the optimal molecular structure is determined using a given method, the energy levels that electrons can occupy can be obtained as a result.

[0131] In this specification, triplet energy refers to the electronic state in a molecule with a spin quantum number of 1. For triplet energy, time-dependent density functional theory (TD-DFT) is used to calculate singlet and triplet energy levels to obtain the characteristics of the excited states of the optimal molecular structure determined using the above methods. Density functional calculations can be performed using the "Gaussian09" package, a commercially available calculation program developed by Gaussian. The B3PW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and the 6-31G* basis set are used for TD-DFT calculations. The 6-31G* basis set is described in the literature "JAPople et al., J.Chem.Phys.56,2257 (1972)". Time-dependent density functional theory (TD-DFT) is used to calculate the energies obtained for the optimal molecular structure determined using density functional theory when the electron arrangement is singlet and triplet.

[0132] According to one embodiment of this specification, in chemical formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted.

[0133] According to one embodiment of this specification, in chemical formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[0134] According to one embodiment of this specification, in Formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms.

[0135] According to one embodiment of this specification, in Formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0136] According to one embodiment of this specification, in chemical formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; unsubstituted or deuterated phenylene; biphenylene; or methyl-substituted divalent fluorene.

[0137] According to one embodiment of this specification, in Formula 1, Ar1 and Ar2 are the same or different from each other and are each independently deuterium; a halogen group; a cyano group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkylsilyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0138] According to one embodiment of this specification, in Formula 1, Ar1 and Ar2 are the same or different from each other and are each independently deuterium; a halogen group; a cyano group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted linear or branched alkylsilyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0139] According to one embodiment of this specification, in Formula 1, Ar1 and Ar2 are the same or different from each other and are each independently deuterium; a halogen group; a cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0140] According to one embodiment of this specification, in Formula 1, Ar1 and Ar2 are the same or different from each other and are each independently deuterium; a halogen group; a cyano group; a linear or branched alkyl group having 1 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0141] According to one embodiment of this specification, in chemical formula 1, Ar1 and Ar2 are the same or different from each other, and are each independently deuterium; F; cyano; methyl; tert-butyl; trimethylsilyl; unsubstituted or substituted phenyl with deuterium, cyano, F, methyl, tert-butyl or trimethylsilyl; unsubstituted or substituted biphenyl; naphthyl; phenanthrene; triphenylene; terphenyl; fluorenyl with methyl or phenyl substitution; or spirodifluorenyl.

[0142] According to one embodiment of this specification, in chemical formula 1, R1 to R16 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0143] According to one embodiment of this specification, in chemical formula 1, R1 to R16 are hydrogen.

[0144] According to one embodiment of this specification, in chemical formula 1, R1 to R16 are deuterium.

[0145] According to one embodiment of this specification, in chemical formula 1, adjacent groups R1 to R8 are bonded to each other to form substituted or unsubstituted aromatic hydrocarbon rings.

[0146] According to one embodiment of this specification, in chemical formula 1, adjacent groups R1 to R8 are bonded to each other to form substituted or unsubstituted benzene rings.

[0147] According to one embodiment of this specification, in chemical formula 1, adjacent groups R1 to R8 are bonded to each other to form a benzene ring.

[0148] According to one embodiment of this specification, in chemical formula 2, T1 to T8 are the same or different from each other, and each is independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted.

[0149] According to one embodiment of this specification, in chemical formula 2, T1 to T8 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[0150] According to one embodiment of this specification, in chemical formula 2, T1 to T8 are the same or different from each other, and each is independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0151] According to one embodiment of this specification, in chemical formula 2, T1 to T8 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0152] According to one embodiment of this specification, in chemical formula 2, T1 to T8 may be the same as or different from each other, and each is independently hydrogen; deuterium; phenyl; or naphthyl.

[0153] According to one embodiment of this specification, in chemical formula 2, L3 and L4 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted.

[0154] According to one embodiment of this specification, in chemical formula 2, L3 and L4 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[0155] According to one embodiment of this specification, in chemical formula 2, L3 and L4 are the same or different from each other and are each independently a direct bond; or unsubstituted or deuterated monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0156] According to one embodiment of this specification, in chemical formula 2, L3 and L4 are the same or different from each other and are each independently a direct bond; or unsubstituted or deuterated monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

[0157] According to one embodiment of this specification, in chemical formula 2, L3 and L4 are the same or different from each other and are each independently a direct bond; or unsubstituted or deuterated phenylene.

[0158] According to one embodiment of this specification, in chemical formula 2, Ar3 and Ar4 are the same or different from each other and are each independently deuterium; or substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0159] According to one embodiment of this specification, in chemical formula 2, Ar3 and Ar4 are the same or different from each other and are each independently deuterium; or substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

[0160] According to one embodiment of this specification, in chemical formula 2, Ar3 and Ar4 are the same or different from each other and are each independently deuterium; or monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, either unsubstituted or deuterated.

[0161] According to one embodiment of this specification, in chemical formula 2, Ar3 and Ar4 are the same or different from each other and are each independently deuterium; or monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, either unsubstituted or deuterated.

[0162] According to one embodiment of this specification, in chemical formula 2, Ar3 and Ar4 are the same or different from each other, and each is independently deuterium; an unsubstituted or deuterated phenyl group; or an unsubstituted or deuterated naphthyl group.

[0163] According to one embodiment of this specification, L51 is O.

[0164] According to one embodiment of this specification, L51 is S.

[0165] According to one embodiment of this specification, G1 and G18 are connected by -L51- to form a substituted or unsubstituted heterocycle.

[0166] According to one embodiment of this specification, G1 and G18 are connected by -L51- to form a substituted or unsubstituted dibenzofuran ring; or a substituted or unsubstituted dibenzothiophene ring.

[0167] According to one embodiment of this specification, G1 and G18 are connected by -O- to form a substituted or unsubstituted dibenzofuran ring.

[0168] According to one embodiment of this specification, G1 and G18 are connected by -S- to form a substituted or unsubstituted dibenzothiophene ring.

[0169] According to one embodiment of this specification, G1 and G18 are connected by -O- to form a dibenzofuran ring.

[0170] According to one embodiment of this specification, G1 and G18 are connected by -S- to form a dibenzothiophene ring.

[0171] According to one embodiment of this specification, in chemical formula 3, L5 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted.

[0172] According to one embodiment of this specification, in chemical formula 3, L5 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[0173] According to one embodiment of this specification, in chemical formula 3, L5 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0174] According to one embodiment of this specification, in chemical formula 3, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0175] According to one embodiment of this specification, in chemical formula 3, L5 is a direct bond; or a phenylene oxide.

[0176] According to one embodiment of this specification, in chemical formula 3, Ar5 is selected from any of the following structures.

[0177]

[0178] In these structures,

[0179] * indicates the site where it bonds to L5 of chemical formula 3.

[0180] At least one of X1 to X3 is N, and the rest are CH.

[0181] At least one of X4 and X5 is N, and the rest are CH.

[0182] Y1 to Y3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0183] y3 is an integer from 1 to 4, and when y3 is 2 or greater, two or more y3 are the same or different from each other.

[0184] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CH.

[0185] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CH.

[0186] According to one embodiment of this specification, X1 to X3 are N.

[0187] According to one embodiment of this specification, either X4 or X5 is N, and the rest are CH.

[0188] According to one embodiment of this specification, X4 and X5 are N.

[0189] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0190] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0191] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0192] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each independently is an unsubstituted or cyano-substituted linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0193] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each independently is an unsubstituted or cyano-substituted linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms.

[0194] According to one embodiment of this specification, Y1 and Y2 may be the same as or different from each other, and each independently is an unsubstituted or methyl- or pyridyl-substituted phenyl; an unsubstituted or cyano-substituted biphenyl; or a terphenyl.

[0195] According to one embodiment of this specification, Y3 is hydrogen.

[0196] According to one embodiment of this specification, chemical formula 1 is selected from any of the following compounds.

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] According to one embodiment of this specification, chemical formula 2 is selected from any of the following compounds.

[0203]

[0204] According to one embodiment of this specification, chemical formula 3 is selected from any of the following compounds.

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] According to one embodiment of this specification, compounds of formulas 1 to 3 can be prepared using starting materials and reaction conditions known in the art. The type and number of substituents can be determined by those skilled in the art through appropriate selection of known starting materials. Furthermore, commercially available materials can be purchased as compounds of formulas 1 to 3.

[0211] According to one embodiment of this specification, the organic light-emitting device may only include the first organic material layer, the second organic material layer, and the light-emitting layer as organic material layers, but it may also include other organic material layers. For example, it may also include other hole injection layers, hole transport layers, electron blocking layers, hole blocking layers, electron transport layers, electron injection layers, etc.

[0212] According to one embodiment of this specification, the organic light-emitting device may further include additional organic material layers. These additional organic material layers may include one or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron control layer, an electron blocking layer, a hole blocking layer, and a hole control layer. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic material layers.

[0213] In another embodiment, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more layers of organic material and a cathode are sequentially laminated on a substrate.

[0214] In another embodiment, the organic light-emitting device can be an inverted organic light-emitting device having a reverse structure in which a cathode, one or more layers of organic material and an anode are sequentially laminated on a substrate.

[0215] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0216] The organic light-emitting devices described in this specification may have, for example, the following characteristics: Figure 1 and Figure 2 The structure shown is not limited to this.

[0217] Figure 1 The structure of an organic light-emitting device in which an anode 2, a first organic material layer 3, a light-emitting layer 4, a second organic material layer 5, and a cathode 6 are sequentially laminated on a substrate 1 is shown. Figure 1 An illustrative structure according to one embodiment of this specification is shown, and may also include other organic material layers.

[0218] Figure 2 The structure of an organic light-emitting device in which an anode 2, a hole injection layer 7, a hole transport layer 8, an electron blocking layer 9, a light-emitting layer 4, a hole blocking layer 10, an electron injection and transport layer 11, and a cathode 6 are sequentially laminated on a substrate 1 is shown. Figure 2 An illustrative structure according to one embodiment of this specification is shown, and may also include other organic material layers.

[0219] The organic light-emitting device described herein can be manufactured using materials and methods known in the art, except that the first organic material layer contains a compound represented by chemical formula 1, the light-emitting layer contains a compound represented by chemical formula 2, and the second organic material layer contains a compound represented by chemical formula 3.

[0220] For example, the organic light-emitting device of this specification can be fabricated by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. In this document, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using physical vapor deposition (PVD) methods such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and then depositing a material suitable for use as a cathode on the organic material layer. Alternatively, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0221] In addition to this method, organic light-emitting devices can also be manufactured by sequentially laminating a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003 / 012890). However, the manufacturing method is not limited to this.

[0222] As an anode material, materials with a large work function are generally preferred, allowing holes to be smoothly injected into the organic material layer. Specific examples of anode materials that can be used in this disclosure include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0223] As cathode materials, materials with a small work function are generally preferred, allowing electrons to be smoothly injected into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al, LiO2 / Al, or Mg / Ag; and so on, but are not limited to these.

[0224] A capping layer for electrode protection can also be formed on the cathode, and those used in the art can be appropriately used as capping layer materials.

[0225] The hole injection layer is a layer that receives holes from the electrode, and as a hole injection material, a compound is preferably one that has the ability to transport holes and thus has a hole injection effect from the anode and an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and, in addition, has excellent thin film forming ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0226] A hole transport layer is a layer that receives holes from a hole injection layer and transports them to a light-emitting layer. As a hole transport material, that is, a material capable of receiving holes from an anode or hole injection layer and moving them to a light-emitting layer, a material with high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0227] An electron blocking layer is a layer that can improve the lifetime and efficiency of a device by preventing holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer. When an organic light-emitting device according to one embodiment of this specification includes an additional electron blocking layer in addition to the electron blocking layer of Formula 1, the additional electron blocking layer can be formed in a suitable portion between the light-emitting layer and the electron injection layer using known materials.

[0228] An electronic control layer may also be disposed between the light-emitting layer and the electron transport layer. Materials used in the art can be appropriately used as the material for the electronic control layer.

[0229] An electron transport layer is a layer that receives electrons from an electron injection layer and transports them to a light-emitting layer. When an organic light-emitting device according to one embodiment of this specification includes an additional electron transport layer besides the one containing formula 3, a material suitable as the electron transport layer material is one that can readily receive electrons from the cathode, move them to the light-emitting layer, and has high electron mobility. Specific examples include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes; and so on, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are common materials with low work functions followed by an aluminum or silver layer. Specifically, these include cesium, barium, calcium, ytterbium, and samarium, and in each case, followed by an aluminum or silver layer.

[0230] An electron injection layer is a layer that injects electrons from the electrode, and preferably contains compounds that possess electron transport capabilities, exhibit an electron injection effect from the cathode, and demonstrate excellent electron injection effects on the light-emitting layer or material, preventing excitons generated in the light-emitting layer from migrating to the hole injection layer, and also possess excellent thin film forming capabilities. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives; metal complexes; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these.

[0231] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0232] The electron injection and transport layer is a layer that simultaneously performs electron injection and transport, and it is a layer that injects electrons from the electrode and transports the electrons to the light-emitting layer. When additional layers are provided in addition to the electron injection and transport layer containing chemical formula 3, the above-mentioned electron transport layer material and electron injection layer material can be used in combination.

[0233] A hole blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as a hole injection layer. Specific examples may include... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0234] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-sided-emitting type.

[0235] The structure of one embodiment of this specification can also be used in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., based on similar principles used in organic light-emitting devices.

[0236] Invention Embodiments

[0237] The fabrication of organic light-emitting devices will be specifically described in the following examples. However, these examples are for illustrative purposes only, and the scope of this specification is not limited thereto.

[0238] Manufacturing of organic light-emitting devices

[0239] Comparative Example 1

[0240] Using a patterned ITO substrate as the anode, a hole injection layer is formed on the ITO substrate using HT1 and HI1 via vacuum deposition. On the hole injection layer, a hole transport layer is formed using the following HT1. Deposit the following HTL_A to the hole transport layer The thickness is used as an electron blocking layer, and the following bodies A and BD are deposited in the electron blocking layer at a volume ratio of 1% to 5%. The thickness is used as the light-emitting layer, and the following HBL is deposited to... The thickness serves as a hole-blocking layer.

[0241] On the hole-blocking layer, ETL_A and LiQ were co-deposited at a mass ratio of 5:5. The thickness serves as the electron injection and transport layer.

[0242] On the electron injection and transport layer, Mg:Ag (10%) was co-deposited to The thickness was then increased, and Al was deposited to... As a cathode.

[0243]

[0244]

[0245]

[0246] Comparative Examples 2 to 6 and Examples 1 to 13

[0247] Organic light-emitting devices of Comparative Examples 2 to 6 and Examples 1 to 13 were manufactured in the same manner as in Comparative Example 1, except that the compounds in Table 1 below were used as electron blocking layers instead of HTL_A, the compounds in Table 1 below were used instead of the body of the light-emitting layer_A, and the compounds in Table 1 below were used instead of the ETL_A of the electron injection and transport layers.

[0248] For Comparative Examples 1 to 6 and Examples 1 to 13, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density, and the results are shown in Table 1 below.

[0249] [Table 1]

[0250]

[0251] Based on the results in Table 1, it was determined that an organic light-emitting device according to one embodiment of this specification, which contains chemical formula 1 in the electron blocking layer, chemical formula 2 as the main body of the light-emitting layer, and chemical formula 3 in the electron injection and transport layers, has superior luminous efficiency compared to organic light-emitting devices containing each of chemical formulas 1 to 3 or only two materials containing chemical formulas 1 to 3.

[0252] Energy level calculation

[0253] The LUMO levels, singlet energies, and triplet energies of compounds HTL_A to HTL_F and ETL_A to ETL_F are shown in Table 2 below.

[0254] [Table 2]

[0255]

[0256] In Table 2, Gaussian 03 (a quantum chemical calculation program developed by Gaussian Corporation of the United States) and density functional theory (DFT) were used to calculate the LUMO level, singlet energy, and triplet energy of the compounds of formula 1 and formula 3 used in Examples 1 to 13 of this specification. For the optimal structure using B3LYP as a function and 6-31G* as a basis function, the calculated value of the triplet energy was obtained using time-dependent density functional theory (TD-DFT).

[0257] The compounds HTL_B to HTL_F and ETL_B to ETL_F in Table 2 satisfy one or more of Formulas 1 to 3, and the organic light-emitting devices are found to have excellent efficiencies as shown in Table 1.

Claims

1. An organic light-emitting device, comprising: anode; cathode; A light-emitting layer disposed between the anode and the cathode; A first organic material layer disposed between the light-emitting layer and the anode; and A second organic material layer is disposed between the light-emitting layer and the cathode. The first organic material layer contains a compound represented by the following chemical formula 1; The light-emitting layer contains a compound represented by the following chemical formula 2; The second organic material layer comprises a compound represented by the following chemical formula 3; and Chemical formula 1 and chemical formula 3 satisfy any one or more of the following [Formula 1] to [Formula 3]: [Chemical Formula 1] In chemical formula 1, L1 and L2 may be the same or different from each other, and each is a direct bond independently; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Ar1 and Ar2 may be the same as or different from each other, and each is independently an unsubstituted or linearly or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and R1 to R16 are hydrogen. [Chemical Formula 2] In chemical formula 2, L3 and L4 are direct bonds; Ar3 and Ar4 may be identical or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and T1 to T6 and T8 are hydrogen; T7 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms. [Chemical Formula 3] In chemical formula 3, At least one of G1 to G18 is -L5-Ar5, and the rest are hydrogen, or G1 and G18 are connected by -L51- to form a heterocycle with O or S; L5 is a direct bond; or a monocyclic or polycyclic arylene group with 6 to 20 carbon atoms; L51 is O; or S. Ar5 is selected from any of the following structures: In the structure, * indicates the site where L5 of chemical formula 3 is bonded; X1 to X3 are N; X4 and X5 are N; Y1 and Y2 may be the same as or different from each other, and each is independently an unsubstituted or cyano-substituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms. Y3 is hydrogen; y3 is 4; as well as [Formula 1] [Equation 2] [Formula 3] In equations 1 to 3, E L1 This refers to the LUMO energy level in eV of the compound represented by chemical formula 1; E L3 This refers to the LUMO energy level in eV of the compound represented by chemical formula 3; E s1 This refers to the singlet energy, expressed in eV, of the compound represented by chemical formula 1. E s3 This refers to the singlet energy, expressed in eV, of the compound represented by chemical formula 3. E T1 This refers to the triplet energy, expressed in eV, of the compound represented by chemical formula 1. as well as E T3 This refers to the triplet energy, expressed in eV, of a compound represented by chemical formula 3.

2. The organic light-emitting device according to claim 1, wherein the first organic material layer is configured to contact the light-emitting layer.

3. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises a fluorescent dopant.

4. The organic light-emitting device according to claim 1, wherein the light-emitting layer is a single layer.

5. The organic light-emitting device according to claim 1, wherein the light-emitting layer is a blue light-emitting layer.

6. The organic light-emitting device according to claim 1, wherein the maximum emission wavelength λ in its emission spectrum is... 最大 The range is from 400 nm to 470 nm.

7. The organic light-emitting device according to claim 1, wherein the light-emitting layer further comprises a compound different from the compound represented by chemical formula 2.

8. The organic light-emitting device according to claim 1, comprising one or more organic material layers between the second organic material layer and the light-emitting layer.

9. The organic light-emitting device according to claim 1, wherein the second organic material layer comprises a compound represented by chemical formula 3, an organoalkali metal complex compound, and a mixture thereof.

10. The organic light-emitting device according to claim 1, wherein chemical formula 1 is selected from any of the following compounds: 。 11. The organic light-emitting device according to claim 1, wherein chemical formula 2 is selected from any of the following compounds: 。 12. The organic light-emitting device according to claim 1, wherein chemical formula 3 is selected from any of the following compounds: 。

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